1,2-Dichloroethane → HCID 86643312, compound

Participants

Reaction Steps

To a suspension of (2-chloropyridin-3-yl)acetic acid (Intermediate 3; 2.0 g, 11.6 mmol) in DCM (100 mL) was added N,O-dimethylhydroxylamine hydrochloride (1.19 g, 12.2 mmol), N-methylmorpholine (3.8 mL, 34.8 mmol) and EDC (2.3 g, 12.2 mmol). The mixture was stirred at room temperature for 48 hours, diluted with DCM (100 mL), washed with 10% HCl (aq) solution (200 mL) and brine (200 mL), dried (Na2SO4), filtered and the solvents removed in vacuo. The crude product was purified by column chromatography (SiO2, 1:1 EtOAc:DCM) to give the title compound as a white waxy solid (2.2 g, 88%). δH (DMSO-d6) 8.31 (1H, dd, J 4.7, 1.9 Hz), 7.81 (1H, dd, J 7.5, 1.9 Hz), 7.40 (1H, dd, J 7.5, 4.7 Hz), 3.93 (2H, s), 3.76 (3H, s), 3.15 (3H, s). LCMS (pH 3) RT 2.22 minutes, (ES+) 215 35Cl (M+H)+, 217 37Cl (M+H)+.

Provenance & Evidence